5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid | 150779-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid
• CAS: 150779-79-6
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: BGJIXAANOBCFEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 5-[2-(2,5-二羟基苯基)乙基]-2-羟基苯甲酸
  参考文献：
  名称：

  Novel Antiproliferative Agents Derived from Lavendustin A

  摘要：

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.

  DOI：

  10.1021/jm00050a005
• 作为产物：
  描述：

  SDZ LAP 977 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  Novel Antiproliferative Agents Derived from Lavendustin A

  摘要：

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.

  DOI：

  10.1021/jm00050a005

文献信息

• Bis(phenyl)ethane derivatives
  申请人：Sandoz Ltd.

  公开号：US05488135A1

  公开（公告）日：1996-01-30

  The invention concerns the compounds of formula I ##STR1## wherein the substituents have various significances, in free form and, where such forms exist, in salt form. The compounds have potent antihyperproliferative/antiinflammatory and anticancer activity.

  本发明涉及公式I的化合物 ##STR1## 其中取代基具有各种意义，包括自由形式和盐形式（如果存在这些形式）。这些化合物具有强效的抗高增殖/抗炎和抗癌活性。
• Bis (phenyl)ethane derivatives
  申请人：SANDOZ LTD.

  公开号：EP0539326B1

  公开（公告）日：1996-04-10
• US5488135A
  申请人：——

  公开号：US5488135A

  公开（公告）日：1996-01-30
• Novel Antiproliferative Agents Derived from Lavendustin A
  作者：Peter Nussbaumer、Anthony P. Winiski、Salvatore Cammisuli、Peter Hiestand、Gisbert Weckbecker、Anton Stuetz

  DOI：10.1021/jm00050a005

  日期：1994.11

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.